


Corrupt

by shoelessmoose



Category: Supernatural
Genre: AU, Destiel - Freeform, Multi, Teen!Benny, Teen!Cas, Teen!Dean, Teen!Garth
Language: English
Status: In-Progress
Published: 2014-06-11
Updated: 2014-07-08
Packaged: 2018-02-04 07:00:57
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 7,597
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1769947
Author URL: https://archiveofourown.org/users/shoelessmoose/pseuds/shoelessmoose
Summary: <blockquote class="userstuff">
              <p>Walker's Boarding School for Boys is among the nation's finest. Those who have graduated from this high school have gone on to attend Yale and Harvard and Stanford. After Dean Winchester was expelled from his previous high school and his name permanently tainted in his home town of Lawrence, Kansas, his mother, Mary, requested a favor from the dean of Walker's Boarding School -- an old family friend. In one phone call, Dean's fate was determined for him. He would spend the duration of his high school years in Kansas City, Missouri attending a "stupid prep school". </p>
<p> </p>
<p>Based on <a href="http://shoelessmoose.tumblr.com/post/88438159508">this</a> tumblr post by faroutxarchive.</p>
            </blockquote>





	1. The Blue-Eyed Boy With Glasses

The pavement ground beneath the tires of John Winchester's 1967 Chevrolet Impala. Mary, his mother, had given Dean the car after his father passed away from a stroke, but now, she was taking it back. Boys at the prep school were not allowed to have vehicles on campus -- only bikes and scooters. Dean huffed defiantly as he stared out the window at the prairie around him. Mary was driving the car and glanced warily over at him before peering in the rearview mirror at the sleeping child in the back.

"Dean, this will be good for you," she said, her voice low so as not to wake Sam. Dean ignored her, flipping on the radio to the classic rock station, barely audible through the static. He fumbled for a cassette tape, stuffing it into the player. Soon he was lost in Metallica. Mary sighed in defeat, pursing her lips. What had she done wrong? Dean had been such a sweet child, but upon entering his teen years he became reckless, paid little attention to his grades, and ultimately destroyed their lives. The only source she could trace his rebellion to was the passing of his father. 

She reached out her hand and grabbed Dean's. "Please don't be mad at me, son," she beckoned gently. But Dean just jerked his hand away, glaring at his mother for a moment before looking back out the window. In the backseat, Sam rustled awake, his hair a mess atop his head. 

"Mom, I need to go to the bathroom," he mumbled, sleepily. The sound of his voice brought a small smile to Dean's face, but he refused to allow Mary to see his weakness. Mary nodded in the rearview mirror and veered off the highway to the next gas station. Sam jumped out of the backseat, running into the store. Dean wanted to go get one of those 42 oz. slushies, but he couldn't bring himself to ask his mother for money. Instead he closed his eyes, leaning his head back against the headrest.

When Sam returned to the car, he brought Dean a slushie, very aware of his big brother's desires. Dean winked at him, rustling the hair on top of his head while Mary pumped the gas. "Thanks, Sammy," Dean said, his first words since they had left Lawrence. Sam nodded as he took a long sip of his own slushie.

"Why do you have to go away?" Sam asked, still not quite understanding why his "celebrity" big brother had to be sent away. Dean shrugged his shoulders. 

"I'm too cool to be seen in the streets," he answered, as if it was the only obvious thing to say. Sam raised his eyebrows and then pushed at Dean's shoulder. 

"Yeah, right!" Both boys were laughing and playing when Mary got back in the car. Dean immediately shut down, turning back toward the front and buckling his seat belt to avoid his mother's nagging voice. 

The rest of the trip was filled with awkward silence and the occasional cassette tape change -- a few were Mary's choice. Mostly The Beatles, which Dean tried to tune out to prevent childhood memories of his mom and dad dancing in the kitchen to Hey Jude. 

When they approached the gate of the school, Dean felt his stomach drop. She was really going to just leave him here like some stray dog. He glanced back at Sam, flashing a reassuring smile, just for his sake. The first stop was the dean's office where Dean received a nice long lecture about appropriate behavior, curfew, and uniforms. He looked over at his mother, raising his eyebrows.

"Uniforms!?" he cried out in frustration, raising his arms up in the air. "Can we just go home?" It wasn't really a question. He was begging. "Please, Mom. I'll do anything." But Mary just smiled sadly at her son, petting his hair. 

"You have to stay, Dean. I'm not doing it to be mean... it's for your own protection." Dean jerked away from her, fighting back his tears. 

"Whatever," he spat. "Where's my room?" he asked the dean. The man stood up and waved down a studious looking boy with black hair. 

"Castiel, this is Dean Winchester. Can you please show him to his dorm? He's in Warren Hall, floor five, room C." Dean stared at Castiel, feeling a strange sensation in the pit of his stomach. Castiel's blue eyes peered over his thick glasses at Dean's green eyes and he blushed, looking back at the dean. 

"Uh... yeah, yeah sure," he muttered under his breath. Dean rolled his eyes. This guy was the king of nerds. He couldn't even answer a question without getting all flustered. Dean looked at his mom and then at Sam who was looking around the halls in admiration. This would be a place out of Sammy's dreams. He was beyond studious, after all. He even stayed after school to tutor other children. 

"Come here, little brother," he said, pulling Sam into a hug. "You take care of Mom, okay?" Sam nodded and then stepped away so Dean could hug Mary. He hesitated for a moment and then threw his arms around her. It wasn't entirely her fault he was here -- even if he did blame her. Plus, he wasn't sure how long it would be until he was able to see them again. Christmas? Later? The thought scared him. Dean watched as Mary and Sam left in his favorite car and then he turned to Castiel, hauling his bag over his shoulder.

"Lead the way..." he said, his voice gruff. Castiel didn't speak a word, just started walking. Dean chuckled under his breath. "It's Castiel, right?" The black haired boy nodded, pushing his glasses up further on his nose and clutching his books tighter to his chest. "So, Cas," Dean started, shortening his name without permission. Castiel peered over his glasses at Dean, raising an eyebrow. No one had ever called him that before, surprisingly. He wanted to tell him to pronounce his entire name, but then he decided it was actually kind of endearing. "What grade are you in?"

"Ninth," Castiel answered, staring up at the taller man, but quickly averting his gaze as soon as they made eye contact. He didn't return the question as most normally would, probably due to the butterflies rising up from his stomach into his throat. Instead, he coughed nervously. Dean smirked. Maybe this wouldn't be so bad after all. He already had a new prospect of his torturing endeavors. 

"I'm a sophomore," Dean said, answering the question Castiel forgot to ask. Cas pulled open the door for him and Dean walked through. In the elevator, the freshman and the sophomore stood awkwardly in silence. On the third floor the doors opened a couple of rowdy boys came bustling into the elevator. One of them had almost golden eyes and he pinched Castiel's ear, laughing as he looked to the other, who had blonde hair and blue eyes. 

"Cassie!" shouted the one who had him by the ear. "Who's your friend?" The doors closed behind them and Dean watched as Castiel squirmed away from the brunette guy.

"Stop it, Gabriel!" he whined, pushing him back. The blonde one smacked Castiel on the back of the head.

"Stop it, Gabriel," he mimicked, laughter erupting from his lips. "Well, don't be rude, Castiel. Introduce us to your friend." Castiel looked at Dean, cheeks flushed with embarrassment, and then back at the two boys. 

"Michael, Gabriel, this is Dean Winchester. He's new here and the dean asked me to show him to his dorm." Castiel's words were all slurred together in an obviously panicked frenzy, which only led Michael and Gabriel to laugh harder. Dean raised his eyebrows up, folding his arms across his chest, obviously unamused with their antics.

"Dean Winchester, it's a pleasure," Gabriel said, sticking out his hand. Dean stared at it for a moment and then back at Gabriel's face.

"I don't shake hands with monsters," he said matter-of-factly. Gabriel stepped back, raising his eyebrows. As he opened his mouth to speak the doors opened behind him. Dean cut him off. "Looks like this is us, Cas. Shall we?" Dean pushed past the two jokesters, hitting Michael with his bag on the way out. It wasn't an accident, but it seemed like one. Just before the doors closed he heard a voice shouting after him.

"You'll regret this, Winchester!" He laughed.

"Bite me!" Castiel looked at him and shook his head, a small smirk on his face.

"That was -- awesome," he said under his breath. Dean just elbowed him lightly.

"Don't worry about those dicks. You got me now." Dean was already falling into place. "How do you know those guys anyway?" 

"They're my brothers," Castiel spat. Dean stopped walking and faced Castiel. Only because Dean had stopped walking did Castiel also quit walking. He adjusted his books in his arms as they were starting to get heavy. Dean stared for a moment longer and then took the books from Cas, readjusting his bag on his shoulder and continued walking.

"You three don't look anything alike," Dean stated as an after thought. Castiel stopped outside of a door labeled C and nodded toward it. 

"Adopted," he answered shortly. "There's your room." Dean stared at the door incredulously.

"So I'll drop off my bag and then take your books back to your room?" Cas sighed, grabbing his books. He looked at his watch and then shoved his glasses back up toward his eyes.

"I'm already fifteen minutes late for my study session," he said with urgency in his voice. "Get unpacked and I'll come get you at dinner." Castiel was already scurrying down the hallway, books clutched to his chest when Dean hollered after him.

"What time is dinner?!" Cas didn't even bother to turn around.

"Six o' clock! And you'll need to be in uniform!" And then he had disappeared around the corner. Dean laughed under his breath and entered into his room. There were two beds, one was obviously owned so Dean plopped his things down on the other bed. He hoped his roommate was at least semi-decent. For a moment he sat at the edge of his bed and cradled his head in his hands, then he decided to go on and unpack. Might as well get comfortable. He was in for the long haul.


	2. The Mess Hall

When Castiel picked Dean up from his room he had another goofy looking guy with him who went by the name of Garth, presumably also a freshman. Dean walked alongside the two of them, listening as they discussed their chemistry homework. It took everything in his power not to roll his eyes at the over zealous students. He liked Cas, but this Garth guy was a little iffy. It was easily a ten minute walk to the cafeteria, which Castiel and Garth kept referring to as "the mess hall." Dean wasn't against a good workout, but working out just to get a meal? That was a little much. He was trying his best to adapt, but then, how could he? He was eating dinner with strangers instead of his kid brother and mother.

After waiting in line Dean was served an overcooked piece of chicken with a side of macaroni and green beans. There was also a piece of stale bread. He grimaced at his plate, homesick for Mary's cooking. Castiel led Dean and Garth to a table in the corner, secluded, like the two boys Dean was with seemed to be. But Dean didn't mind. He was happy to have company. Dean slid his tray across the table, taking a seat, before glancing back and forth between Garth and Cas. He laughed, poking at his chicken.

"So how's a guy supposed to get laid around here, huh?" Dean glanced around at the sausage fest before looking back at Garth and Cas. His stupid grin dissipated from his face when he noticed that Castiel averted his gaze, shoveling his mouth full of macaroni and cheese, while Garth raised an eyebrow at him. Dean exhaled heavily. His friends at his old school had been much cooler. But Dean had made Castiel his personal mission. He could turn that boy out in no time. His roomie, though? Garth seemed to be another story. In fact, in Dean's eyes, Garth was the competition.

Dean made eye contact with Gabriel from across the mess hall, who was making fists in the air in his direction and elbowing Michael wildly. Michael's laughter erupted through the mess hall, as if Gabriel's fists were the funniest thing in the world to exist. Dean winked over at the brothers before turning his attention back to Cas. Castiel had turned to look at Gabriel and Michael and then back at Dean just in time to see him wink. Once again, Castiel's cheeks flushed red and Dean felt his stomach flip flop. Why did that get to him so much? Castiel opened his mouth to speak, but Garth was faster.

"I wouldn't mess with those two," he stated, as if Dean was asking for trouble in a mere wink. Dean scoffed, taking a bite of his chicken. The flavor was great but the cook really needed to learn timing in the kitchen. A few minutes less and the chicken would have been superb. 

"Those dickbags don't scare me," Dean replied before he had entirely finished his bite. Garth looked down at his plate in disgust, but Castiel grinned from ear to ear. Dean winked at Cas, kicking his leg under the table. "They don't scare Cas either," Dean mentioned. Garth looked up from his plate, eyebrows furrowed together as he looked back and forth between Castiel and Dean.

"Cas?" He stated. "Why didn't I think of that nickname?" Garth threw his hands up in defeat, turning his body slightly toward Castiel. "Dude, I've been trying to name you forever! And it was so simple all along." Dean's laughter erupted from his lips before he could tell himself not to laugh. Garth shot a warning glance at Dean, which of course only triggered more laughter. Garth was no match for Dean. He might have been a little fiesty, but Dean wasn't just a whole lotta bark with no bite. He had been to juvie for crying out loud.

"Any name other than Cassie will do," Cas answered shortly before stuffing some mac and cheese in his mouth. Garth half smiled, looking over at Dean. 

"So have you gotten your class schedule yet?" Dean raised his eyebrows, shaking his head. "You should probably do that before Monday. Mrs. Harvelle's office is open tomorrow from eleven to three." Before Dean could respond, Gabriel was standing beside him, grabbing him by the ear. Dean jumped up from his plate, swatting Gabriel's hand away and glaring at him, hands curled into fists at his side. He straightened out his back and narrowed his eyes.

"If you _ever_ touch me again," he started, but before he could finish Gabriel was already laughing, backing away with his hands up. 

"Calm down, butch," he said, his words a little shaky. Castiel watched, wide-eyed as Gabriel ceased his torment. "I was just having a little fun. Damn, son." Dean ground his teeth together, his jaw line hardening.

"I'm not your son and I'm sure as hell not your playtoy in this cat and mouse game you think you have going on." Dean didn't move until Gabriel started walking away, then he fell back into his seat. "Dickbag," he muttered under his breath, choosing not to make eye contact with either Garth or Castiel. After a few moments of silence he looked up from his plate.

"So Mrs. Harvelle? She's my counselor?" Dean asked, resuming the conversation as if nothing had happened. Castiel was happy to pretend nothing had happened -- that was his way, after all.

"Yeah. All the boys in Warren Hall report to her. She's nice. You'll like her." Dean winked at Cas.

"Yeah, but is she hot?" Garth situated himself in his seat, leaning forward. 

"She's intimidating as all hell, but she _is_ pretty attractive for an older woman." Garth shrugged sitting back. "Her husband is the football coach, though. So I'd be careful what you say." Garth eyed the group of jocky looking boys sitting just a few tables over from them. Dean just laughed.

"You sure do seem to be worried about a lot," Dean retorted. "Me? I'm not scared of nobody." 

"Anyone," Castiel corrected. Dean flushed red for a split second before regaining his cocky composure. 

"Yeah, yeah, brain."

When dinner came to a close, Castiel and Garth walked Dean back to his room. Dean was sad to lose his company, but he was definitely happy to get out of the khaki pants he was required to wear. They just weren't as comfortable as his jeans or pajama pants that he often wore to his old school. 

Inside the room, Dean found that his roommate had returned. The guy was sitting on his bed, a book open, but he was looking past it at something on the wall. Dean turned to look and noticed a photo of his family. Sentimental type. That was okay, though, because Dean had put a picture of his family on his nightstand. The guy didn't even try to say hi to Dean, so Dean took the initiative.

"Um, hi. I'm Dean," he stuck out his hand. Only then did the boy's blue eyes meet with Dean's. He stared at his hand for a moment and then shook it. 

"I'm Benny. Benny Lafitte." Dean smiled as he plopped down on his bed, noticing a phone between their beds.

"Does that line dial out of state?" Benny glanced at the phone and back at Dean.

"Homesick, already?" Dean nodded slowly, unsure of if he could trust his roommate with his weaknesses. Benny smiled warmly.

"That line only calls within the campus. If you need to reach anywhere else, you'll have to use the payphones. There's some on the first floor." Benny checked his watch. "But it's already 8 PM, so there's probably a line for them. By the time you get dialed out it'll be curfew. And I promise you, boy. You don't want to be caught out past curfew on your first night here." Out? He would still be in his dorm? Was this place really that strict?

Dean groaned and banged his head against the wall. "Promised my kid brother I'd call tonight." Benny smiled knowingly as he stared back up at the photo on the wall. His arms were around a young girl's shoulder, presumably his little sister.

"You'd do best to call him in the early morning. You're allowed out of your room as early as five, but no one ever is except for the nerdy boys." Benny closed his book, sitting it on the nightstand as he rolled onto his side. He propped his head up on his arm, staring at Dean.

"So what's your story, huh? Why'd your family abandon you in this prison?" Dean raised his eyebrows. He thought that this school was all about the prep boys and their rich parents wanting to make sure they got a quality education. But if that were true, then how did Benny know that his family didn't want him around anymore? 

"Aren't we all just here for a good education?" Dean said, tilting his head to the side. Benny chuckled.

"I suppose some of these boys are. Yuppie parents and what not. But not you... you don't seem the type," Benny answered, his southern drawl ringing in Dean's ears. Was he that obvious? Or maybe it was because Benny was the same. Either way, Dean felt like he could trust this guy, although he wasn't sure why.

"I got in some trouble at my old school. My mom sent me here. The dean did her a favor," Dean said, his words like venom. Benny nodded, knowingly.

"Yeah. I got expelled from all the schools in my district," Benny answered shortly, his eyes hazing over. "So my dad sent me away. Makes sense, I guess." Dean raised his eyebrows. The guy was a little off, but didn't seem like he was too much trouble. What could he have done? Benny noticed the surprise on Dean's face and chuckled a bit.

"I haven't always been this cute and cuddly," he said, his voice low. Dean heard footsteps in the hallway and doors opening and closing, boys laughing and talking. He lie back on the bed and stared up at the ceiling. "You go to mess hall tonight?" Benny asked as an afterthought. 

"Yeah, why? Didn't you?" Dean answered, his gaze averting back to Benny. Benny shook his head. 

"I only go on certain nights. I've got a pantry stocked in here." Benny stood up and opened a cabinet full of boxed foods and bags of chips. "So if you're ever feeling like avoiding the tragedy that is mess hall, you're welcome to a snack, bunkie." Dean laughed and nodded.

"Yeah, thanks." They remained silent for a long while before Dean had a thought. "Hey, Benny?" Benny had already started dozing off to sleep, but he heard Dean's voice.

"Mmm?" He answered.

"You know where Mrs. Harvelle's office is? I need to get my schedule tomorrow." Benny yawned and Dean listened as his bed creaked.

"I'll walk you there tomorrow." Dean nodded, but mostly to himself since Benny was facing the other way. It was only nine o' clock and Benny was already going to sleep. This place must really take its toll. Dean sighed, watching shadows on the ceiling for the next few hours before finally drifting to sleep himself.


	3. The Bike

“Alright, this is your stop,” Benny said, his southern accent ringing in Dean’s ears. Dean stared at the small trailer among a bunch of other trailers which didn’t seem to belong on campus. This was where all the teacher’s offices were according to Benny. Strange.

The Sunday morning sun reflected off the tin roofs, causing Dean to squint his eyes. He flashed a smile at Benny, waving as the boy walked away. Benny had a bike, but since Dean didn’t, Benny had kindly offered to walk him to Mrs. Harvelle’s office.

Dean stepped to the door, rapping his knuckles against it. A voice, muffled through the door, beckoned him in. Dean took a seat in front of the brunette woman, who, for her age, was actually really attractive. Dean kicked himself for thinking such thoughts, reminding himself how he got in this mess to begin with. He glanced down at his wrinkled khakis and dirty tennis shoes. Tennis shoes were a violation of dress code, but Dean didn’t really care at this point in time. 

His eyes slowly made their way up to Mrs. Harvelle, who was glancing at his shoes, a small smirk on her face. “Have a seat, boy,” she said, motioning to the plush chair in front of her desk. Dean was shocked that she hadn’t mentioned his shoes, but her facial expression indicated that she had acknowledged them and he already knew what words she would say, therefore she didn’t need to mention them.

“Winchester, right?” Dean scratched the back of his head and raised his eyebrows inquisitively. Apparently the woman had a great deal of intuition.

“Uh, yeah,” he answered, gruffly. She nodded, pulling a file from her desk.

“We don’t get many newcomers that aren’t freshman, so you stick out like a sore thumb,” she answered, as if reading his mind. She tapped her pen against the desk as she quickly perused his file, her eyebrows perking up occasionally. Dean strained to see what she was reading about him, but the handwriting was hardly legible right side up, much less upside down. When she was finished reading, she set her pen down, folding her hands on the desk in front of her.

“Alright, so you’re not the best performer academically,” she started, her voice slightly stern. But then her eyes softened and a small smile formed on her lips. “I imagine you’ve had quite a bit to deal with in your life, though. I was friends of your father.” She leaned back in her chair. “You look quite a lot like him. Got his attitude, too.” Dean’s eyes opened wide. She had known dad? But how? Why had he never heard of her?

“Neat,” he muttered sarcastically, adjusting his facial expression to fit his choice of apathy. He wasn’t interested in having a damn pity party. He just wanted to get his schedule and get the hell out of there. Mrs. Harvelle nodded slowly, recognizing that Dean had no intention of carrying on a real conversation with her. 

“Listen up, kid,” she said, her voice returning to the stern, motherly voice that had gotten under Dean’s skin only moments ago. “You don’t have to talk to me if you don’t want to. But I expect none of this monkey business you had going on at your previous schools, ya hear?” Dean nodded, swallowing the lump in his throat. Damn, that woman could be scary. “The courses here are harder than those public schools, so you’re really gonna have to hunker down and learn the material.” Mrs. Harvelle rustled through the paperwork on her desk, returning her reading glasses to her face.

“It looks like you passed Algebra I with a B, so I’m putting you in Geometry. It’s the next level math course.” Dean watched as she scribbled something on a piece of paper. “You’ll be meeting with Mr. Henrickson for classes every weekday at 8 AM, sharp. Don’t be late,” she warned, peering over her glasses. “Henrickson loves detention.” Dean rolled his eyes. Math? First thing in the morning? Well that was just fucking beautiful.

“You’ll be taking English Language and Composition with Ms. Mosely at nine o’ clock,” she continued. “Do you have a map of campus?” Dean shook his head, kicking his foot against her desk, which obviously annoyed her. “Quit fidgeting!” Dean immediately stilled.

“Your math class in the general academic building, but your English course is in Voertman’s Hall.” Mrs. Harvelle slid the map across the desk, circling each building. Dean noticed they were literally across campus from each other. “You’re going to have to haul ass, for lack of a better phrase.” Dean chuckled at her curse word. “Got a bike?” 

Dean almost said yes, since, at home, he did have a bike. He and his mother, however, had not considered that a bike would be useful on campus. Once again, he cursed the spur of the moment decision to send him away. Finally, he shook his head in defeat.

“You any good with mechanics?” At the mention of mechanics, Dean’s eyebrows shot up. He nodded eagerly. “Alright, well I’ve got an old bike one of the seniors a few years ago left behind. It’s a little rusted up, needs some TLC and it’ll be like new. You interested?” 

“Yes, thank you,” he replied, his first nice words since he entered the office. Mrs. Harvelle seemed scary, especially when she used her stern voice, but Dean could tell she was soft at heart, and generous, too. She smiled and returned back to his scheduling.

“You’ll need to pick an elective, too. Here’s a list of your choices.” Mrs. Harvelle slid the list across to him. Dean browsed over the choices which included art and choir, not exactly his forte, but also gym and weightlifting. Dean opted for weightlifting. It was something that would keep his body occupied without making him want to shoot some coach screaming about a final lap. Mrs. Harvelle composed the rest of Dean’s schedule and then stood up.

“Come on. Let’s go get that bike.” Dean followed Mrs. Harvelle, the two of them walking in silence, until they reached a little fenced in garden. The bike was propped against the back fence, and Mrs. Harvelle had been right. It did need a good deal of work. 

Dean glanced around the garden for a moment. “You grow this stuff?” Mrs. Harvelle nodded, proud of her small garden. 

“It’s something to pass the time when there aren’t students banging down my door.” Dean chuckled, walking toward the bike and wheeling it carefully around the plants. The tires were a little flat, but he was still able to roll it easily enough. It would be a great bike in no time.

“Thanks, Mrs. Harvelle,” Dean said, his voice small.

“Please,” she said, slapping him on the shoulder. “Call me Ellen.” Dean nodded.

“Ellen,” he repeated. 

Dean, remembering the route Benny had taken him to Ellen’s office, walked himself back to his dorm, his bike thudding along with him. He passed many faces, some familiar from dinner the previous evening, some that he had never seen. Most stared and pointed and whispered as he passed, but Dean clenched his jaw and ignored them. 

As he rounded the corner to Warren Hall, he was met face to face with a familiar blue-eyed boy. His glasses were falling down his nose, so Dean could see his eyes clearly over the black rim. The black-haired boy lit up when he saw Dean, smiling from ear to ear, which sent Dean’s heart racing. But naturally, he played it cool.

“What’s up, Cas?” Dean looked the boy up and down, leaning his bike against the stone sign which indicated that Warren Hall was up ahead. “I got my schedule,” he beamed as he pulled it from his pocket. He assumed that he and the freshman would not share many, if any classes, but he was proven wrong, as Castiel snatched the schedule from his hand.

“We’ve got math, history, _and_ English together!” Cas mused, the excitement clear in his voice. Dean raised an eyebrow.

“But those are sophomore classes,” he retorted. Castiel simply laughed. 

“I’m advanced,” he beamed. Dean rolled his eyes, scoffing.

“Whatever, brains. We got lunch together?” Cas glanced at Dean’s lunch schedule and then looked back up, shaking his head. 

“Only on the weekends, I guess.” They stood in silence for a moment as Castiel eyed Dean’s bike. “That thing looks like shit,” he said, finally. Dean’s eyes sparked at the tiny little expletive from the freshman’s lips. He dropped his jaw in shock.

“Casti _el_ ,” Dean slurred, emphasizing the end of his name. “Who knew you had such a mouth on you?” Cas slapped Dean’s shoulder playfully, but Dean felt like an electric current had rocked his body. 

“There’s more where that came from,” Cas joked. _Yeah, I’ll bet,_ Dean thought.

“Well, if you’ll excuse me… I have a shitty bike to repair.” Castiel nodded, slinging his backpack over his shoulder and trekking away. Dean turned and watched as the messy-haired boy disappeared around the corner, then he turned his attention the bike.

Several hours later, Dean was becoming frustrated. He didn’t have the tools he needed to properly repair the bike. He knew better than to even attempt to blow up the tires with his mouth and the can of coke he purchased from the vending machine was proving inefficient for the amount of rust on the bike’s chain. He was scrubbing at the chain with a coke soaked toothbrush when an older man in a trucker hat stopped to watch. 

Dean glanced up, wiping the sweat from his brow with the back of his arm. “Can I help you?” he asked, gruffly. The man laughed.

“Probably not, but I can help you.” The man stooped to the ground beside Dean, grabbing his towel and rubbing it against the chain. He glanced at the red residue on the towel. “I’m Mr. Singer,” he said. “I teach shop class.” Dean raised his eyebrows. Ellen hadn’t mentioned a shop class at all. “The coke is good for dissolving rust, but it dries quickly and makes it hard to remove the residue since coke is naturally sticky… What you need is some vinegar. And this towel is not the right kind of towel for the job.” Dean rolled his eyes, an expression he realized he was making a lot more since he had been here than ever before.

“Well, duh. But I only have access to the soda machine and the bath towels. Most teenage boys don’t keep vinegar in their pantries,” Dean retorted, sarcasm lacing his voice. Mr. Singer obviously found this amusing, because his boisterous laugh filled the air around them. Dean grumbled, returning his attention to the bike. He attempted to turn the pedals, cringing at the squealing of the rusted, unlubricated chain and bearings. “And I need some damn WD-40 and a tire pump.”

“Watch your mouth, kid,” Mr. Singer quipped, despite the smile that was still on his face. “Tell ya what. Bring that bike by my shop before dinner and we’ll fix it up for ya.” He slapped Dean on his shoulder, the second adult to do that in a day. Mr. Singer rose to his feet and Dean stood next to him. “You registered for my shop class? I could use a guy like you in there.” Dean shook his head.

“I woulda registered if Ell… Mrs. Harvelle had given me the option in my electives. But I’m taking stupid weightlifting.” Mr. Singer nodded, knowingly.

“You ain’t a junior yet, are ya?” Dean just shook his head in response, glancing down at his desolate bike.

“Sophomore.” Mr. Singer smiled at Dean and then took another look at the bike.

“Good work so far. I’ll see you tonight.” 

As Mr. Singer walked away toward the center of campus, Dean couldn’t help but wonder how a guy like him even got a teaching position. He wasn’t nearly as professionally dressed as the other teachers and administrators he had seen so far. He had a dirty old baseball cap on, for fuck’s sake. And he didn’t even speak proper English. Not that Dean did most of the time, but wasn’t that sort of the gig for prep school teachers? You have to be able to talk like a textbook? 

Dean laughed to himself, flipping the bike back onto its flat tires. He rolled it over to a bike stand and locked it up – not that anyone would try to steal this piece of crap. And if they did they’d stand out like a sore thumb. Dean contemplated going for a walk, exploring the campus, discovering the escape routes, but he opted out for a nice hot shower. As the water beat down over his skin, washing the dirt and rust away, Dean started to feel like maybe he could get used to life around here. But then he remembered that classes would start the next day and a wave of nausea washed over him. How was he supposed to play hooky when he lived at the school?


	4. The Shop

**Summary for the Chapter:**

> Dean meets Mr. Singer in his shop and spends some quality time with Castiel.

Mr. Singer’s shop had a surprisingly clean interior in comparison to the ramshackle exterior. There were two or three vehicle frames visible outside of the shop, in addition to several bikes of different makes and sizes. Dean didn’t knock on the door, just walked right in, since he had been invited. Immediately his nostrils filled with the scent of motor oil and gasoline. It took him back to his days working in his father’s auto shop. 

_“Dean, hand me that wrench wouldya? And bring me a beer, son!” John’s voice echoed in Dean’s mind. Young Dean nodded and grabbed a wrench, placing it in his father’s hand, glancing at the engine. It was a Chevy Small-Block engine, something that Dean knew a little about even at the age of five. John glanced up at him, flashing a smile which illuminated his white teeth in contrast to the grease on his face. “Beer?” he repeated._

_Dean ran out of the garage and to the office area, staring up at the neon sign which read “Winchester Auto Repair: Saving People from Fixing Things”. Dean beamed at the family business, his father’s namesake._

Dean remembered when they took down the name Winchester and the catchy little slogan and renamed it Meineke. It wasn’t long after his father’s stroke and Mary, with little money to pay the bills, had to sell the shop. Dean didn’t come out of his room for a week after that, entirely devastated.

Mr. Singer beckoning for Dean to bring his bike over to the stand pulled Dean from his nostalgia. He forced a smile onto his face and walked his bike forward, before flipping it over. As Dean and Mr. Singer got to work on the two-wheeled vehicle, neither of them spoke except to ask the other for a tool. In less than an hour the bike was looking great.  
“Thanks, Mr. Singer,” Dean said, sticking out his hand. Bobby took his hand, giving it a firm shake.

“Anytime, boy. Hey, if you wanna paint this baby up, I got some cans in that drawer over there,” Mr. Singer added as he wiped his hands on a towel. Dean nodded enthusiastically pulling out the drawer. He dug around for a green can, but found a bottle of Johnnie Walker Blue Label instead. He pulled it out, a smirk on his face as he inspected its contents. Mr. Singer grunted, displeased that the boy had found his stash. Dean spun the cap and smelled the bottle just as Mr. Singer came and snatched it from his hands.

“You always go sniffin’ old men’s whiskey?” Mr. Singer asked.

“Only when it’s Johnnie Walker,” Dean quipped. He knew a thing or two about drinking. His father had actually given him his first beer, but it wasn’t until after his death that Dean really started drinking and mixing up with the wrong crowd. He had even smoked marijuana few times and took a liking to cigarettes. Bobby raised his eyebrows.

“Now, kid, I read your file. And I won’t have any of that mischief here,” Mr. Singer warned. Now it was Dean’s turn for his eyebrows to perk up.

“So what does the file say? This kid’s poison, right?” Dean plopped down on a work bench as Bobby eyed him carefully, watching as the emotion flashed through his eyes, despite his already hardened exterior. “That no good, dirty scoundrel, Winchester boy. Might as well stick him in Juvie now ‘cause he’ll be in prison at eighteen. Ain’t nothin’ good ever come from a boy like that. Summer school Winchester, eh?” Dean was no stranger to the things people said about him – he just wished it didn’t bother him so much. He opted out of meeting Mr. Singer’s gaze. Instead he stared at his torn up sneakers until he felt a hand on his shoulder.

“I assume a ‘no good scoundrel’ like yourself knows a good bit about engines, yeah?” Bobby’s voice was laced with sarcasm, as if he knew that Dean was anything but the words he used to describe himself. “I got this truck over here I’m trying to get runnin’,” he said, leading Dean toward it and popping up the hood. Dean inspected the engine, before looking up at Bobby.

“Well, Mr. Singer, you know these big-block engines have a lot of transmission issues. Have you replaced that yet?” Bobby smiled from ear to ear, nodding.

“I already tried that, but I’m impressed, Winchester. Looks like your father trained you right.” At Mr. Singer’s mention of his father, Dean’s mouth went metallic, his eyes opened wide. It was at that moment that Mr. Singer decided he would not tell Dean that he knew John Winchester very well, just yet. Bobby shrugged, pouring himself a glass of whiskey and then pouring another, smaller glass.

“Can you keep a secret, kid?” Dean nodded, taking the glass in his hand as he looked at the truck. He and Bobby worked side by side on the truck for over an hour before Bobby clapped his hand on Dean’s back and mentioned getting on to the mess hall. 

Dean grabbed his bike on the way out the door and then turned around. “Thanks again, Mr. Singer!” Bobby smiled and tipped his hat at Dean, before leaning back over the truck. Dean smiled to himself as he hopped on his newly painted back and rode it toward the mess hall. He considered changing his clothes first, but decided against it. 

He was nearly to the mess hall when he saw Castiel walking alone, his blue eyes glistening in the setting sun. It wasn’t until Dean got closer that he noticed the red rings around Cas’ eyes. For a moment he was furious, but instead of acting over protective, he decided to distract him instead. 

“Hey, angel eyes!” Dean shouted out, his smile wide. Castiel looked up and couldn’t help but smile when he saw Dean’s new and improved bike. “You’re going the wrong way. Food’s that way,” Dean bellowed, even though he was close enough to Cas now not to scream. Castiel just shook his head.

“I’m not really that hungry,” he muttered, glancing down at his feet. “Your bike looks good,” he added as an afterthought. Dean felt his stomach grumble, but if Castiel wasn’t eating, then he wasn’t either. 

“Well hop on!” Castiel laughed and climbed up onto the handle bars. Dean stared at the fit figure in front of his eyes, his breath catching before he composed himself. “You ready?” he asked, his voice a little huskier than he had intended. Cas nodded and Dean went to peddling, riding them all around campus before noticing a secluded area near the football field. He slowed the bike down and watched as Cas jumped down, his eyebrows furrowing together.

“Uh… Dean? What are we doing here?” Dean shrugged, hopping off the bike himself and walking it toward the fence. Castiel followed him instinctively, mesmerized by Dean’s inexplicable actions for some reason. Dean climbed onto the fence, sitting on the ledge and staring out at the football field. Castiel followed him up just in time to see Dean dig in his jacket pocket and pull out a pack of cigarettes. His eyes grew wide.

“You smoke?” he asked, his voice a little more high pitched than usual. Dean nodded, lighting himself one and then offering another to Castiel. Cas shook his head vehemently.  
“Suit yourself,” Dean said between slow drags on his cigarette. He kicked his feet against the fence, waiting for Castiel to tell him that smoking was a disgusting habit and he was gonna get himself killed or some other medical, smart boy nonsense that Dean didn’t care to here. But Castiel remained silent, staring up at the moon in the still sunlit sky.

“You ever wonder what’s out there?” Castiel asked as Dean flicked his cigarette into the grass. For a moment Dean was puzzled until he followed Castiel’s gaze to the sky. He sighed.

“Dunno,” he answered shortly. “I mean, my mom always told me there were angels watching over me,” he continued, but his sentenced lingered in the air, as if unfinished. Castiel glanced over at Dean, who’s mouth hung slack-jawed.

“But…?” He prodded.

“But I mean… how can you really know?” Dean added. “I mean, as far as I’m concerned, if angels are real, they’re all a bunch of dicks.” Castiel erupted with laughter which was contagious to Dean.

“I think my parents would have to disagree with you,” Castiel chimed once his laughter had subsided. “I mean, myself and all of my siblings are named after angels.” Dean nodded.  
“Yeah, I noticed,” he replied, just before his stomach began to grumble again. Castiel eyed him, his blue orbs squinting as he inspected the older Winchester brother.

“Why didn’t you go to dinner if you’re hungry?” he asked, trying to sound complacent about it, but sounding more like a worried parent. Dean simply shrugged.

“You looked like you needed some company,” was his only reply.

“Well you weren’t wrong,” Castiel admitted.

“Wanna talk about it?” Dean’s question took Castiel by surprise. Dean just didn’t seem like the ‘talk it out’ type. But either way, Cas wasn’t really up to talking about his problems. Besides, they would probably sound miniscule to Dean, who seemed as if he had been through so much.

“Not really,” he answered. “We should be getting back. Almost curfew.” Dean stared at Castiel, a small smirk on his face, a bit too long for comfort. Finally Castiel spoke, “What? Why are you looking at me like that?” Dean chuckled.

“Are you always so quick to follow the rules?” he inquired as he hopped down from the fence. Castiel followed him down and shook his head.

“Only on school nights.” Dean laughed, knowing that Castiel was lying. The kid had probably never broken a rule in his life. Dean had every intention of breaking Castiel and turning him bad, but for tonight, he was already nervous about classes and really just wanted to sleep. He peddled them back to their dorm building and latched his bike to the rack.

“Good night, Cas. See you bright and early for math?” Cas nodded, waving at Dean.

“Night, Dean.” Dean smiled as he let himself into his room to find Benny not present. He laughed to himself, realizing that Benny was probably out getting some. Dean undressed and cuddled up into his sheets, looking at the picture of his mom and brother on his bedside table. The last thought he had before drifting off to sleep was of Castiel’s blue eyes glistening with tears, red and swollen. His heart ached.


End file.
